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Catechol → N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide

HRID 433724
ノート
印刷プレビュー

反応式

HRID 433724 の反応式
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[F:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24](F)=[CH:23][C:22]=1[NH:31][C:32](=[O:34])[CH3:33]>O>[F:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24]([O:2][C:1]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])=[CH:23][C:22]=1[NH:31][C:32](=[O:34])[CH3:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 289CatecholHCID 6228Dimethylformamide2 回HCID 11430Potassium CarbonateHCID 14624893N-(2,5-Difluoro-4-nitrophenyl)acetamide

生成物 1

HCID 21933568N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide収率 83.7%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
60 °C

実験手順

1.1 g of catechol and 2.76 g of potassium carbonate were added to 20 ml of N,N-dimethylformamide, and the mixture was heated to 60° C. Into this mixture was added dropwise a solution comprising 2.16 g of N-(2,5-difluoro-4-nitrophenyl)acetamide and 10 ml of N,N-dimethylformamide at temperatures from 65 to 70° C. The temperature of the mixture was kept for 1 hour, then, the mixture was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic layer was washed with dilute hydrochloric acid, washed with water, dried over magnesium sulfate, concentrated, and the resulted crystal was washed with t-butyl methyl ether to obtain 2.56 g of N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide.

後処理

  1. additionInto this mixture was added dropwise a solution
  2. customfrom 65 to 70° C
  3. temperaturethe mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with dilute hydrochloric acid
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. washthe resulted crystal was washed with t-butyl methyl ether

出典と根拠

ORDレコード
ord-cf223cd60e114f12ba91a5fa83033a92
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06667413B2

反応ノート

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